International patent application PCT/EP2010/055666 (publication number WO2010/125082) describes compounds having the general formula (I):

wherein
R1′ is 9- or 10-membered bicyclic heteroaryl wherein the 9- or 10-membered bicyclic heteroaryl contains from one to three heteroatoms independently selected from oxygen and nitrogen and is optionally substituted by C1-6alkyl, C3-6cycloalkyl, halo, —CN or —NHSO2R5′, or
pyridinyl optionally substituted by one or two substituents independently selected from C1-6alkyl, —OR6′, halo and —NHSO2R7′;
R2′ and R3′, together with the nitrogen atom to which they are attached, are linked to form a 6- or 7-membered heterocyclyl wherein the 6- or 7-membered heterocyclyl optionally contains an oxygen atom or a further nitrogen atom and is optionally substituted by one or two substituents independently selected from C1-6alkyl;
R4′ is hydrogen or methyl;
R6′ is hydrogen or C1-4alkyl; and
R5′ and R7′ are each independently C1-6alkyl, or phenyl optionally substituted by one or two substituents independently selected from halo;
and salts thereof.
The examples of WO2010/125082 describe the preparation of 6-(1H-indol-4-yl)-4-(5-{[4-(1-methylethyl)-1-piperazinyl]methyl}-1,3-oxazol-2-yl)-1H-indazole which may be represented by the formula (II):
hereinafter referred to as “Compound A” and the hydrochloride salts thereof, and the preparation of N-[5-[4-(5-{[(2R,6S)-2,6-dimethyl-4-morpholinyl]methyl}-1,3-oxazol-2-yl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide which may be represented by the formula (III):
hereinafter referred to as “Compound B” and the (R)-mandelate salt thereof.
International patent application PCT/EP2011/068604 (publication number WO2012/055846) describes a novel polymorph of Compound A and salts of Compound A and polymorphs thereof, processes for their preparation, pharmaceutical compositions comprising them, and their use in the treatment of various disorders.
International patent application PCT/EP2011/065419 (publication number WO2012/032067) describes novel polymorphs and salts of Compound B, processes for their preparation, pharmaceutical compositions comprising them, and their use in the treatment of various disorders.
The processes for preparing Compounds A and B described in WO2010/125082, WO2012/055846 and WO2012/032067 are unsuitable for manufacturing the compounds on a commercial scale. For example, one of the methods described uses a stannane reagent in the key oxazole-indazole coupling step. Stannane reagents are typically toxic and environmentally harmful. An alternative process which avoids the use of a stannane reagent is described in WO2012/055846. However, this process requires a significant number of steps, starts from expensive starting materials and has a poor overall yield.
There therefore remains a need to develop an improved process for preparing Compounds A and B which may be suitable for use on a commercial scale.